KN05. P. J. Perez – The reactivity of alkanes toward organometallic electrophiles

Effectenbeurszaal, ground floor July 11, 2017 14:00 - 14:30

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Prof. Pedro J. Pérez

The functionalization of alkanes and, particularly, methane, yet constitutes an area of interest given the relatively low number of catalytic systems reported to date toward that end [1]. The large availability of methane in natural or shale gas deposits makes it an excellent C1-source for synthetic purposes, albeit the catalytic systems described to date do not meet the required activity (TON (minimum) = 1 s-1) for industrial uses[2].

Our group has been involved in the area of hydrocarbon C-H functionalization using the strategy of carbene transfer from diazo compounds,[3] which along the years has been developed until methane could be reached[4]. In this contribution an account of such development, including the importance of the reaction medium and the nature of the carbon-hydrogen bond in the reaction outcome will be presented. An extensive study of relative reactivity of a number of alkanes, from C1 to C8 has led to a model that allows the estimation of the reactivity based on a few simple rules.

[1] P. J. Pérez,Alkane C-H Activation by Single-Site Metal Catalysis, Springer, Dordrecht, 2012.
[2] A. Caballero, P. J. Pérez, Chem. Soc. Rev. 2013, 42, 8809-8820.
[3]A. Caballero, M. M. Díaz-Requejo, M. R. Fructos, A. Olmos, J. Urbano, P. J. Pérez, Dalton Trans. 2015, 44, 20295-20307.
[4] A. Caballero, E. Despagnet-Ayoub, M. M. Díaz-Requejo, A. Díaz-Rodríguez, M. E. González-Núñez, R. Mello, B. K. Muñoz, W. Solo Ojo, G. Asensio, M. Etienne and P. J. Pérez, Science, 2011, 332, 835–838.